20469-65-2Relevant articles and documents
A high yield, selective synthesis of 1,3,5-trimethoxybenzene
Ji, Ya-Fei,Zong, Zhi-Min,Wei, Xian-Yong
, p. 225 - 227 (2003)
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Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation
Murphy, Jaclyn M.,Liao, Xuebin,Hartwig, John F.
, p. 15434 - 15435 (2008/09/19)
We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B2pin2, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step. Copyright
Grindstone chemistry: (Diacetoxyiodo)benzene-mediated oxidative nuclear halogenation of arenes using NaCl, NaBr or I2
Karade,Tiwari,Huple,Siddiqui
, p. 366 - 368 (2007/10/03)
A technique of "Grindstone chemistry" is applied to the solvent-free halogenation of arenes with NaCl, NaBr or I2 using (diacetoxyiodo)benzene as the oxidant. Improved yields and higher purities of the products are observed compared with those from established methods.